37

Colonial Homes for Sale in Kent County MD

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  • 200 School St, Millington, MD 21651
    200 School St, Millington, MD 21651
    200 School St, Millington, MD 21651
    /33

    $398,000

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft

    200 School St, Millington, MD 21651

    Warm and Welcoming 3-Bedroom Colonial with a Private Backyard and spacious primary suite.Come home to the comfort and charm of this inviting 3-bedroom, 2.5-bath Colonial, tucked into a peaceful country setting while still offering convenient access to points north. From quiet mornings to busy afternoons and relaxed evenings, this home provides a warm, easy-flowing layout designed for everyday

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    200 School St, Millington, MD 21651
  • 102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    102 Little Harbor Way, Chestertown, MD 21620
    /23

    $839,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    102 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    102 Little Harbor Way, Chestertown, MD 21620
  • 36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    36 Landing Ln, Chestertown, MD 21620
    /26

    $753,500

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    36 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    36 Landing Ln, Chestertown, MD 21620
  • 104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    104 Landing Ln, Chestertown, MD 21620
    /24

    $813,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,192 Sq Ft

    104 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    104 Landing Ln, Chestertown, MD 21620
  • 8184 Rock Hall Rd, Chestertown, MD 21620
    8184 Rock Hall Rd, Chestertown, MD 21620
    8184 Rock Hall Rd, Chestertown, MD 21620
    /38

    $38,200,000

    • 4 Beds
    • 2 Baths
    • 2,330 Sq Ft

    8184 Rock Hall Rd, Chestertown, MD 21620

    Tulip Forest, a farm defined by scale, stewardship, and long-term value. Recognized as a premier sporting estate, this legacy holding property is the kind of asset that seldom comes to market on Maryland's Upper Eastern Shore. 1,054 +/- acres held intact under one ownership: 680 tillable acres, 272 acres of timber, 5 ponds, 3 impoundments, 26.75-acre wetlands restoration project, 45 acres CRP, a

    Joe Hickman Cross Street Realtors LLC

    8184 Rock Hall Rd, Chestertown, MD 21620
  • 14046 Tockwogh Ln, Galena, MD 21635
    14046 Tockwogh Ln, Galena, MD 21635
    14046 Tockwogh Ln, Galena, MD 21635
    /54

    $1,595,000

    • 4 Beds
    • 2 Baths
    • 2,538 Sq Ft

    14046 Tockwogh Ln, Galena, MD 21635

    Enjoy sweeping water views, a bulkheaded shoreline, and a lawn extending to the water's edge—an exceptional and hard-to-find combination. Boating enthusiasts will appreciate the private dock, complete with a boat lift and Jet Ski lift and the location on the river. This charming four-bedroom home blends timeless character with everyday functionality. The thoughtfully designed floor plan features

    Christopher McClary Gunther-McClary Real Estate

    14046 Tockwogh Ln, Galena, MD 21635
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /18

    $295,000

    • 1 Bed
    • 1 Bath

    117 N Water St Unit 3B, Chestertown, MD 21620

    Set within a stately 1800s waterfront home, this beautifully renovated one-bedroom condominium offers an effortless life along the Chester River. Begin your mornings with river views, spend shaded afternoons beneath the trees, or retreat to the floating dock for sunbathing and quiet reflection. With an updated kitchen and bath, kayak storage, off-street parking, and downtown Chestertown’s shops

    Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 212 Washington Ave, Chestertown, MD 21620
    212 Washington Ave, Chestertown, MD 21620
    /2

    $675,000

    Open House 10/03 Coming Soon Oct 3
    • 5 Beds
    • 3 Baths
    • 2,838 Sq Ft

    212 Washington Ave, Chestertown, MD 21620

    Welcome home to historic Chestertown. This beautiful 5 bedroom colonial is located just one block from Washington College. Relax on your welcoming mahogany front porch before stepping inside this pristine home. Features a beautifully updated kitchen. Fresh exterior paint gleams. Iconic slate roof adds timeless appeal. Enjoy the private, fenced backyard oasis, meticulously landscaped for outdoor

    Mary Carlisle Coldwell Banker Chesapeake Real Estate Company

    212 Washington Ave, Chestertown, MD 21620
  • 123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    123 Trafford Dr, Chestertown, MD 21620
    /45

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 2,504 Sq Ft

    123 Trafford Dr, Chestertown, MD 21620

    Space, convenience, and value just minutes from downtown Chestertown! This spacious 4-bedroom, 2.5-bath Colonial in Coventry Farms checks the boxes for buyers looking for room to spread out without giving up convenience.The main level features a comfortable living room, dining area, kitchen, and half bath. Upstairs, you’ll find four bedrooms, including a spacious primary suite with a

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    123 Trafford Dr, Chestertown, MD 21620
  • 206 Maplewood Ln, Galena, MD 21635
    206 Maplewood Ln, Galena, MD 21635
    206 Maplewood Ln, Galena, MD 21635
    /29

    $363,000

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    206 Maplewood Ln, Galena, MD 21635

    Welcome to Galena a little big town. Located just down the road from the Sassafras River this area has excellent access to the Chesapeake Bay, shopping, restaurants and more. With just about an hours drive you can be in Baltimore, Philadelphia or Annapolis. What an opportunity to build instant equity. Spacious home in great community, backing to farmland. This home is located in the community,

    Kristie Midash L. C. Parker Real Estate

    206 Maplewood Ln, Galena, MD 21635
  • 129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    129 Trafford Dr, Chestertown, MD 21620
    /15

    $480,000

    • 3 Beds
    • 2.5 Baths
    • 3,176 Sq Ft

    129 Trafford Dr, Chestertown, MD 21620

    PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effortless entertaining, this home offers spacious interiors filled with abundant natural light.The main level features a bright kitchen with Breakfast Bar that flows seamlessly into a sunny Florida room, creating the perfect space

    Teresa Queen Elevated Real Estate Solutions

    129 Trafford Dr, Chestertown, MD 21620
  • 117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
    /73

    $1,500,000

    $100K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 5,400 Sq Ft

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620

    **Listing price is for FOUR units for sale as an investment package!117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, 1B, 2A, & 2B, Chestertown, MD 21620
  • 115 Metcalf Rd, Chestertown, MD 21620
    115 Metcalf Rd, Chestertown, MD 21620
    115 Metcalf Rd, Chestertown, MD 21620
    /10

    $259,900

    New Construction Open Thu 6PM - 7PM
    • 3 Beds
    • 1.5 Baths
    • 1,280 Sq Ft

    115 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you'll find generously sized bedrooms including a large primary suite with

    David Moore Real Broker, LLC

    115 Metcalf Rd, Chestertown, MD 21620
  • 106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    106 Landing Ln, Chestertown, MD 21620
    /24

    $799,900

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,092 Sq Ft

    106 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 3.5 baths. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. There's also a private study, which could be used as additional space

    Julia Hilfiker Gunther-McClary Real Estate

    106 Landing Ln, Chestertown, MD 21620
  • 12118 Still Pond Creek Rd, Worton, MD 21678
    12118 Still Pond Creek Rd, Worton, MD 21678
    12118 Still Pond Creek Rd, Worton, MD 21678
    /35

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 2,322 Sq Ft

    12118 Still Pond Creek Rd, Worton, MD 21678

    Welcome to your dream home in Worton, MD! This stunning center hall Colonial-style property boasts 4 bedrooms, 2.5 bathrooms, and sits on over 6 acres of picturesque land. As you approach the home, you'll be greeted by a charming circular driveway and an oversized detached 2 car garage, perfect for storing all your vehicles and outdoor equipment. Inside, the home features beautiful hardwood

    Angela Allen Patterson-Schwartz-Hockessin

    12118 Still Pond Creek Rd, Worton, MD 21678
  • 37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    37 Landing Ln, Chestertown, MD 21620
    /24

    $765,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    37 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath

    Julia Hilfiker Gunther-McClary Real Estate

    37 Landing Ln, Chestertown, MD 21620
  • 117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    117 N Water St Unit 2B, Chestertown, MD 21620
    /23

    $350,000

    • 1 Bed
    • 1 Bath
    • 850 Sq Ft

    117 N Water St Unit 2B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2B, Chestertown, MD 21620
  • 21123 Striper Run, Rock Hall, MD 21661
    21123 Striper Run, Rock Hall, MD 21661
    21123 Striper Run, Rock Hall, MD 21661
    /36

    $389,900

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,040 Sq Ft

    21123 Striper Run, Rock Hall, MD 21661

    ROCK HALL — ON THE GRID, NOT OFF THE GRID! Discover Eastern Shore living in this beautifully maintained end-unit townhome offering 2,040+ sq ft, a flexible floor plan and a premium oversized lot—with NO HOA! The standout feature is the oversized rear sunroom/4th bedroom, larger than the primary suite, with its own private exterior entrance and direct kitchen access. Ideal as a guest room, home

    susan taylor Chaney Homes, LLC

    21123 Striper Run, Rock Hall, MD 21661
  • 103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    103 Sutton Way, Chestertown, MD 21620
    /53

    $550,000

    • 5 Beds
    • 3.5 Baths
    • 3,816 Sq Ft

    103 Sutton Way, Chestertown, MD 21620

    103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and

    Liddy Campbell TTR Sotheby's International Realty

    103 Sutton Way, Chestertown, MD 21620
  • 11960 Flour Mill St, Kennedyville, MD 21645
    11960 Flour Mill St, Kennedyville, MD 21645
    11960 Flour Mill St, Kennedyville, MD 21645
    /53

    $515,000

    • 7 Beds
    • 5 Baths
    • 3,836 Sq Ft

    11960 Flour Mill St, Kennedyville, MD 21645

    Welcome to 11960 Flour Mill Street. This is the perfect house for a growing family or a multi-generational household. Main House has 6 full bedrooms and 4 full bathrooms while the second floor above the garage is a spacious mother-in-law suite with a separate entrance, efficiency kitchen, full bath and walk-in closet. First floor has a bedroom and full bath and wide open floor plan in the kitchen

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    11960 Flour Mill St, Kennedyville, MD 21645
  • 25133 Smithville Rd, Worton, MD 21678
    25133 Smithville Rd, Worton, MD 21678
    25133 Smithville Rd, Worton, MD 21678
    /35

    $357,997

    $2K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,208 Sq Ft

    25133 Smithville Rd, Worton, MD 21678

    Welcome to 25133 Smithville Rd.! This spacious 4-bedroom, 3-bath traditional Colonial offers comfortable living with plenty of room to spread out. The main level features a desirable primary suite with a private full bath, along with an inviting eat-in kitchen and formal dining room perfect for everyday living and entertaining.Step outside to enjoy the spacious, level backyard with

    Alyson Anderson Allfirst Realty, Inc.

    25133 Smithville Rd, Worton, MD 21678
  • 121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    121 Metcalf Rd, Chestertown, MD 21620
    /10

    $264,900

    New Construction
    • 3 Beds
    • 1.5 Baths

    121 Metcalf Rd, Chestertown, MD 21620

    Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with white shaker cabinets, granite countertops, and stainless steel appliances, plus a covered patio off the kitchen for outdoor enjoyment. Upstairs you’ll find generously sized bedrooms including a large primary suite with walk-in

    David Moore Real Broker, LLC

    121 Metcalf Rd, Chestertown, MD 21620
  • 35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    35 Landing Ln, Chestertown, MD 21620
    /26

    $786,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    35 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the great room with gas fireplace, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like

    Julia Hilfiker Gunther-McClary Real Estate

    35 Landing Ln, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /70

    $499,999

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    MOTIVATED SELLER - BRING OFFERS. Listing will be removed September 30 until Spring 2027. Welcome to 103 Landing Lane: a meticulously maintained 2-bedroom townhome in the desirable waterfront community of Chester River Landing. Just a short walk or bike ride into downtown Chestertown, this elegant, turn-key home offers maintenance-free living, great amenities, and easy water access to the Chester

    Joseph Ciganek Coldwell Banker Chesapeake Real Estate Company

    103 Landing Ln, Chestertown, MD 21620
  • 106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    106 S Queen St, Chestertown, MD 21620
    /92

    $829,000

    $36K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 2,472 Sq Ft

    106 S Queen St, Chestertown, MD 21620

    Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic DistrictThe Bedingfield Hands House, circa 1750, is more than a home—it's a living piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make

    Maryn LeClair Chesapeake Real Estate Associates, LLC

    106 S Queen St, Chestertown, MD 21620
  • 234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    234 N College Ave, Chestertown, MD 21620
    /3

    $85,000

    $35K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,296 Sq Ft

    234 N College Ave, Chestertown, MD 21620

    Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their vision to life. With classic colonial charm, this property offers the perfect canvas for renovation or

    Anastasia Zivkovic Palmer Cummings & Co. Realtors

    234 N College Ave, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /24

    $375,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 316 Middle St, Millington, MD 21651
    316 Middle St, Millington, MD 21651
    316 Middle St, Millington, MD 21651
    /11

    $25,000

    • 672 Sq Ft

    316 Middle St, Millington, MD 21651

    ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 10/2/2026, 10:00 AM. Bidding ends 10/6/2026, 12:40 PM. The list price is the suggested opening bid. Deposit: $5,000.This two-story detached house is located in Millington, MD within Kent County. Residents can enjoy the nearby attractions and facilities such as the Waterfront

    Adam Shpritz Ashland Auction Group LLC

    316 Middle St, Millington, MD 21651
  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /46

    $685,000

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft

    117 N Water St Unit 1A, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 21232 Rock Hall Ave, Rock Hall, MD 21661
    21232 Rock Hall Ave, Rock Hall, MD 21661
    21232 Rock Hall Ave, Rock Hall, MD 21661
    /37

    $325,000

    $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    21232 Rock Hall Ave, Rock Hall, MD 21661

    Welcome to this beautifully renovated 2-bedroom, 2-bath home sitting on a very large lot. This home in Rock Hall, a historic harbor town celebrated for its Chesapeake Bay shoreline, boating lifestyle and vibrant coastal charm, features 2 bedrooms, 2 bathrooms and 1200 square feet. It offers luxury vinyl floors, energy efficient windows, a spacious central island with seating, stainless steel

    Chris Traczyk RE/MAX Advantage Realty

    21232 Rock Hall Ave, Rock Hall, MD 21661
  • 122 S Main St, Galena, MD 21635
    122 S Main St, Galena, MD 21635
    122 S Main St, Galena, MD 21635
    /50

    $384,000

    $36K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 1,684 Sq Ft

    122 S Main St, Galena, MD 21635

    WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot.The exterior features a detached oversized two-car garage with pull-through access to the HUGE

    John Carroll Village Real Estate Company LLC

    122 S Main St, Galena, MD 21635
  • 21384 E Sharp St, Rock Hall, MD 21661
    21384 E Sharp St, Rock Hall, MD 21661
    21384 E Sharp St, Rock Hall, MD 21661
    /22

    $370,000

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft

    21384 E Sharp St, Rock Hall, MD 21661

    Quintessential Rock Hall home with an abundance of charm! Located in the heart of Rock Hall, a short distance to Main Street shops, many fantastic restaurants, and seven marinas. Enjoy evenings and mornings on the screened porch, which runs the expanse of the home. Entering from the porch, you'll find a cosy living room and a galley kitchen with open dining space. This home offers a first-floor

    Julia Hilfiker Gunther-McClary Real Estate

    21384 E Sharp St, Rock Hall, MD 21661
  • 25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    25 Landing Ln, Chestertown, MD 21620
    /22

    $1,099,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,784 Sq Ft

    25 Landing Ln, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 2,784 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 4 bedrooms and 3.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. There is a first floor primary bedroom for one-floor living

    Julia Hilfiker Gunther-McClary Real Estate

    25 Landing Ln, Chestertown, MD 21620
  • 8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    8620 Park Dr, Chestertown, MD 21620
    /66

    $489,900

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,524 Sq Ft

    8620 Park Dr, Chestertown, MD 21620

    Two Story Colonial on 1.37+/- acre lot, rectangular 200 x 300 ft. Approximately 2,700 sq ft. of living area in house (estimate). 4 bedrooms, 2.5 Bathrooms. ½ basement with laundry room and fix-it shop/work bench with 2 crawl spaces. Attached two-car garage with abundant built-in shelving and free-standing cabinets for lots of storage space with garage door opener on each of 2 doors.Forced

    Doug Ashley Doug Ashley Realtors, LLC

    8620 Park Dr, Chestertown, MD 21620
  • 104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    104 Little Harbor Way, Chestertown, MD 21620
    /23

    $849,900

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,980 Sq Ft

    104 Little Harbor Way, Chestertown, MD 21620

    **To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms and 2.5 baths. Inside, an open-concept main level connects the living space, with cozy gas fireplace, to the gourmet kitchen and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath, large

    Julia Hilfiker Gunther-McClary Real Estate

    104 Little Harbor Way, Chestertown, MD 21620
  • 8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    8796 Maryland Pkwy, Chestertown, MD 21620
    /60

    $1,495,000

    $155K PRICE DROP
    • 9 Beds
    • 6.5 Baths
    • 4,776 Sq Ft

    8796 Maryland Pkwy, Chestertown, MD 21620

    Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the National Star-Spangled Banner Trail and just a mile from the Chesapeake Bay, this storied property offers a once-in-a-generation chance to own one of the region's most beloved historic estates.The grounds unfold past

    Tracy Stone Coldwell Banker Chesapeake Real Estate Company

    8796 Maryland Pkwy, Chestertown, MD 21620
  • 117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    117 N Water St Unit 1B, Chestertown, MD 21620
    /20

    $200,000

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft

    117 N Water St Unit 1B, Chestertown, MD 21620

    117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects

    Liddy Campbell TTR Sotheby's International Realty

    117 N Water St Unit 1B, Chestertown, MD 21620
Maryland

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